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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014643
Secondary Accession Numbers
  • HMDB14643
Metabolite Identification
Common NameTolmetin
DescriptionTolmetin is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory agent (anti-inflammatory agents, NON-steroidal) similar in mode of action to indomethacin. [PubChem]The mode of action of tolmetin is not known. However, studies in laboratory animals and man have demonstrated that the anti-inflammatory action of tolmetin is not due to pituitary-adrenal stimulation. Tolmetin inhibits prostaglandin synthetase in vitro and lowers the plasma level of prostaglandin E in man. This reduction in prostaglandin synthesis may be responsible for the anti-inflammatory action. Tolmetin does not appear to alter the course of the underlying disease in man.
Structure
Data?1582753202
Synonyms
ValueSource
1-Methyl-5-(4-methylbenzoyl)-pyrrole-2-acetic acidChEBI
1-Methyl-5-p-toluoylpyrrole-2-acetic acidChEBI
5-(p-Toluoyl)-1-methylpyrrole-2-acetic acidChEBI
TolmetinaChEBI
TolmetineChEBI
TolmetinoChEBI
TolmetinumChEBI
1-Methyl-5-(4-methylbenzoyl)-pyrrole-2-acetateGenerator
1-Methyl-5-p-toluoylpyrrole-2-acetateGenerator
5-(p-Toluoyl)-1-methylpyrrole-2-acetateGenerator
Anhydrous tolmetin sodiumHMDB
Sodium anhydrous, tolmetinHMDB
TolectinHMDB
Tolmetin sodiumHMDB
Anhydrous, tolmetin sodiumHMDB
Dihydrate tolmetin sodiumHMDB
Sodium, tolmetinHMDB
Tolmetin sodium anhydrousHMDB
Tolmetin sodium, anhydrousHMDB
Tolmetin sodium, dihydrateHMDB
Chemical FormulaC15H15NO3
Average Molecular Weight257.2845
Monoisotopic Molecular Weight257.105193351
IUPAC Name2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid
Traditional Nametolmetin
CAS Registry Number26171-23-3
SMILES
CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)
InChI KeyUPSPUYADGBWSHF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-phenylketones
Alternative Parents
Substituents
  • Aryl-phenylketone
  • Benzoyl
  • Toluene
  • Monocyclic benzene moiety
  • N-methylpyrrole
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point156 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.13 g/LNot Available
LogP2.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available158.717http://allccs.zhulab.cn/database/detail?ID=AllCCS00001329
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.81ALOGPS
logP2.73ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.96ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.39 m³·mol⁻¹ChemAxon
Polarizability27.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.81231661259
DarkChem[M-H]-159.73431661259
DeepCCS[M+H]+164.59930932474
DeepCCS[M-H]-162.24130932474
DeepCCS[M-2H]-195.12730932474
DeepCCS[M+Na]+170.69230932474
AllCCS[M+H]+159.632859911
AllCCS[M+H-H2O]+155.632859911
AllCCS[M+NH4]+163.332859911
AllCCS[M+Na]+164.332859911
AllCCS[M-H]-162.032859911
AllCCS[M+Na-2H]-161.832859911
AllCCS[M+HCOO]-161.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TolmetinCN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C13472.9Standard polar33892256
TolmetinCN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C12091.0Standard non polar33892256
TolmetinCN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C12296.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tolmetin,1TMS,isomer #1CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[Si](C)(C)C)N2C)C=C12362.3Semi standard non polar33892256
Tolmetin,1TBDMS,isomer #1CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)N2C)C=C12651.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tolmetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-3930000000-6c43d7fafa7e68cf9c552017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tolmetin GC-MS (1 TMS) - 70eV, Positivesplash10-032i-9442000000-7726560133a119872ef92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tolmetin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolmetin LC-ESI-QQ , positive-QTOFsplash10-0a4i-0090000000-5053b1021a81c4668b542017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolmetin LC-ESI-QQ , positive-QTOFsplash10-014i-0910000000-7cb6eb9d5a42f35eb4bc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolmetin LC-ESI-QQ , positive-QTOFsplash10-014i-0900000000-9898c207cc31a596d3192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolmetin LC-ESI-QQ , positive-QTOFsplash10-014l-6900000000-439955132bb3d3d37cf72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolmetin LC-ESI-QQ , positive-QTOFsplash10-0006-9200000000-aed48305fd97ea83af6d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolmetin LC-ESI-IT , positive-QTOFsplash10-014i-1900000000-3399455ef4fbd98a64d32017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 10V, Positive-QTOFsplash10-0a4l-0090000000-3838af75b0622946263b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 20V, Positive-QTOFsplash10-014i-0950000000-f1c503badfc8847c75e82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 40V, Positive-QTOFsplash10-014l-6900000000-075fb92a19ab89905ba32016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 10V, Negative-QTOFsplash10-0a4i-0090000000-5613b7d02b59ebbf2b1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 20V, Negative-QTOFsplash10-0bt9-1290000000-494f40e70f911873c7282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 40V, Negative-QTOFsplash10-006y-9730000000-49d63827f01b8620343f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 10V, Negative-QTOFsplash10-03di-0090000000-6a704ffbf3202179ae4b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 20V, Negative-QTOFsplash10-01ox-8390000000-db73eded70ef5ae974532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 40V, Negative-QTOFsplash10-0006-5900000000-f83dcdc322966fec3da82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 10V, Positive-QTOFsplash10-0a4i-0190000000-71c82a0a228a88e32b6d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 20V, Positive-QTOFsplash10-066u-1890000000-018d899ab34427dfd79d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin 40V, Positive-QTOFsplash10-0006-9720000000-7eec80edd3ab412a096d2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00500 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00500 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00500
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5308
KEGG Compound IDC07149
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTolmetin
METLIN IDNot Available
PubChem Compound5509
PDB IDNot Available
ChEBI ID71941
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Burdan F, Szumilo J, Klepacz R, Dudka J, Korobowicz A, Tokarska E, Cendrowska-Pinkosz M, Madej B, Klepacz L: Gastrointestinal and hepatic toxicity of selective and non-selective cyclooxygenase-2 inhibitors in pregnant and non-pregnant rats. Pharmacol Res. 2004 Nov;50(5):533-43. [PubMed:15458776 ]
  2. Capasso A, Sorrentino L: Arachidonic acid and its metabolites are involved in the expression of morphine dependence in guinea-pig isolated ileum. Eur J Pharmacol. 1997 Jul 9;330(2-3):199-204. [PubMed:9253954 ]
  3. Kirkova M, Alexandova A, Kesiova M, Todorov S: In vivo effects of amtolmetin guacyl on lipid peroxidation and antioxidant defence systems. Comparison with non-selective and COX-2 selective NSAIDs. Auton Autacoid Pharmacol. 2007 Apr;27(2):99-104. [PubMed:17391279 ]
  4. Kennedy JH, Korn N, Thurston RJ: Prostaglandin levels in seminal plasma and sperm extracts of the domestic turkey, and the effects of cyclooxygenase inhibitors on sperm mobility. Reprod Biol Endocrinol. 2003 Oct 9;1:74. [PubMed:14613550 ]
  5. Capasso A: Further studies on the involvement of the arachidonic acid cascade in the acute dependence produced by mu, kappa and delta opioid agonists in isolated tissues. Neuropharmacology. 1999 Jun;38(6):871-7. [PubMed:10465690 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Capasso A, Sorrentino L: Arachidonic acid and its metabolites are involved in the expression of morphine dependence in guinea-pig isolated ileum. Eur J Pharmacol. 1997 Jul 9;330(2-3):199-204. [PubMed:9253954 ]
  2. Kennedy JH, Korn N, Thurston RJ: Prostaglandin levels in seminal plasma and sperm extracts of the domestic turkey, and the effects of cyclooxygenase inhibitors on sperm mobility. Reprod Biol Endocrinol. 2003 Oct 9;1:74. [PubMed:14613550 ]
  3. Capasso A: Further studies on the involvement of the arachidonic acid cascade in the acute dependence produced by mu, kappa and delta opioid agonists in isolated tissues. Neuropharmacology. 1999 Jun;38(6):871-7. [PubMed:10465690 ]
  4. Burdan F, Szumilo J, Marzec B, Klepacz R, Dudka J: Skeletal developmental effects of selective and nonselective cyclooxygenase-2 inhibitors administered through organogenesis and fetogenesis in Wistar CRL:(WI)WUBR rats. Toxicology. 2005 Dec 15;216(2-3):204-23. Epub 2005 Sep 22. [PubMed:16182428 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563 ]